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Human Metabolome Database Version 2.5

 

Showing metabocard for 7a-Hydroxy-cholestene-3-one (HMDB01993)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-05-22 15:17:31
Update Date 2009-07-21 12:54:14
Accession Number HMDB01993
Secondary Accession Numbers HMDB01331
Common Name 7a-Hydroxy-cholestene-3-one
Description 7a-Hydroxy-cholestene-3-one is a metabolite in bile acid synthesis. It is derived from 7a-hydroxy-cholesterol and can be further metabolized to 7a,12a,-dihydroxy-cholest-4-en-3-one. Analysis of 7a-Hydroxycholestene-3-one (HCO) in serum may serve as a novel, simple, and sensitive method for the detection of bile acid malabsorption in patients with chronic diarrhea of unknown origin (PMID 9952217)
Synonyms
  1. 7 alpha-3ox-C
  2. 7 alpha-hydroxy-4-cholesten-3-one
  3. 7-Hydroxycholest-4-en-3-one
  4. 7a-Hydroxy-4-cholesten-3-one-12alpha
  5. 7alpha-Hydroxy-4-cholesten-3-one
  6. 7alpha-Hydroxycholest-4-en-3-one
  7. Cholest-4-en-7alpha-ol-3-one
  8. HCO
  9. 7-alpha-hydroxy-4-cholesten-3-one
  10. 7-a-hydroxy-4-cholesten-3-one
  11. 7-alpha-hydroxycholest-4-en-3-one
  12. 7-a-hydroxycholest-4-en-3-one
Chemical IUPAC Name (7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Chemical Formula C27H44O2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Cholesterols and derivatives
Class
  • Steroids and Steroid Derivatives
Sub Class
  • Ketosteroids
Family
  • Mammalian Metabolite
Species
  • ketone
  • secondary alcohol
  • alkene
Biofunction
  • Hormones, Membrane component
Application
—
Source
  • Endogenous
Average Molecular Weight 400.637
Monoisotopic Molecular Weight 400.334137
Isomeric SMILES CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)CC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
Canonical SMILES CC(C)CCCC(C)C1CCC2C3C(O)CC4=CC(=O)CCC4(C)C3CCC12C
KEGG Compound ID C05455 Link Image
BioCyc ID Not Available
BiGG ID 45848 Link Image
Wikipedia Link HCO Link Image
NuGOwiki Link HMDB01993 Link Image
Metagene Link HMDB01993 Link Image
METLIN ID 6419 Link Image
PubChem Compound 123743 Link Image
PubChem Substance 7851430 Link Image
ChEBI ID Not Available
CAS Registry Number 3862-25-7
InChI Identifier InChI=1/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h15,17-18,21-25,29H,6-14,16H2,1-5H3/t18-,21-,22+,23+,24-,25+,26+,27-/m1/s1
Synthesis Reference Alexander, David L.; Fisher, Jed F. A convenient synthesis of 7a-hydroxycholest-4-en-3-one by the hydroxypropyl-b-cyclodextrin-facilitated cholesterol oxidase oxidation of 3b,7a-cholest-5-ene-3,7-diol. Steroids (1995), 60(3), 290-4.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 1.69e-04 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 5.46 [Predicted by ALOGPS]; 6.5 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane (Predicted from LogP)
  • Cytoplasm
  • endoplasmic reticulum
Biofluid Location
  • Blood
  • Urine
Tissue Location
Tissue References
Liver —
Concentrations (Normal)
Biofluid Urine
Value 109.8 +/- 16.44 umol/mmol creatinine
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Ge RL, Babb TG, Sivieri M, Resaland GK, Karlsen T, Stray-Gundersen J, Levine BD: Urine acid-base compensation at simulated moderate altitude. High Alt Med Biol. 2006 Spring;7(1):64-71. [PubMed Link Image]
Concentrations (Abnormal)
Biofluid Blood
Value 0.033 +/- 0.011 uM
Age Adult:>18 yrs old
Sex Both
Condition Gallbladder disease
Comments Not Available
References
  • Hillebrant CG, Axelson M, Bjorkhem I, Wang FH, Nyberg B, Einarsson C: Effects of short-term treatment with pravastatin on the hepatic synthesis of cholesterol and bile acids in gallstone patients. Eur J Clin Invest. 1998 Apr;28(4):324-8. [PubMed Link Image]
Associated Disorders
Condition References
Gallbladder disease
  • Hillebrant CG, Axelson M, Bjorkhem I, Wang FH, Nyberg B, Einarsson C: Effects of short-term treatment with pravastatin on the hepatic synthesis of cholesterol and bile acids in gallstone patients. Eur J Clin Invest. 1998 Apr;28(4):324-8. [PubMed Link Image]
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Bile Acid Biosynthesis SMP00035 Link Image map00120 Link Image
General References
  1. Lin RC, Fillenwarth MJ, Du X: Cytotoxic effect of 7alpha-hydroxy-4-cholesten-3-one on HepG2 cells: hypothetical role of acetaldehyde-modified delta4-3-ketosteroid-5beta-reductase (the 37-kd-liver protein) in the pathogenesis of alcoholic liver injury in the rat. Hepatology. 1998 Jan;27(1):100-7. [PubMed Link Image]
  2. Skrede S, Bjorkhem I, Buchmann MS, Hopen G, Fausa O: A novel pathway for biosynthesis of cholestanol with 7 alpha-hydroxylated C27-steroids as intermediates, and its importance for the accumulation of cholestanol in cerebrotendinous xanthomatosis. J Clin Invest. 1985 Feb;75(2):448-55. [PubMed Link Image]
  3. Axelson M, Bjorkhem I, Reihner E, Einarsson K: The plasma level of 7 alpha-hydroxy-4-cholesten-3-one reflects the activity of hepatic cholesterol 7 alpha-hydroxylase in man. FEBS Lett. 1991 Jun 24;284(2):216-8. [PubMed Link Image]
  4. Skrede S, Bjorkhem I: A novel route for the biosynthesis of cholestanol, and its significance for the pathogenesis of cerebrotendinous xanthomatosis. Scand J Clin Lab Invest Suppl. 1985;177:15-21. [PubMed Link Image]
  5. Skrede S, Buchmann MS, Bjorkhem I: Hepatic 7 alpha-dehydroxylation of bile acid intermediates, and its significance for the pathogenesis of cerebrotendinous xanthomatosis. J Lipid Res. 1988 Feb;29(2):157-64. [PubMed Link Image]
  6. Sauter GH, Munzing W, von Ritter C, Paumgartner G: Bile acid malabsorption as a cause of chronic diarrhea: diagnostic value of 7alpha-hydroxy-4-cholesten-3-one in serum. Dig Dis Sci. 1999 Jan;44(1):14-9. [PubMed Link Image]
  7. Brydon WG, Nyhlin H, Eastwood MA, Merrick MV: Serum 7 alpha-hydroxy-4-cholesten-3-one and selenohomocholyltaurine (SeHCAT) whole body retention in the assessment of bile acid induced diarrhoea. Eur J Gastroenterol Hepatol. 1996 Feb;8(2):117-23. [PubMed Link Image]
  8. Wikipedia Link Image
Metabolic Enzymes
  1. 3-oxo-5-beta-steroid 4-dehydrogenase
  2. Aldo-keto reductase family 1, member D1
Enzyme 1 [top]
Enzyme 1 ID 5822
Enzyme 1 Name 3-oxo-5-beta-steroid 4-dehydrogenase
Enzyme 1 Synonyms
  1. Delta(4-3- ketosteroid 5-beta-reductase
  2. Aldo-keto reductase family 1 member D1
Enzyme 1 Gene Name AKR1D1
Enzyme 1 Protein Sequence >3-oxo-5-beta-steroid 4-dehydrogenase 
MDLSAASHRIPLSDGNSIPIIGLGTYSEPKSTPKGACATSVKVAIDTGYRHIDGAYIYQN
EHEVGEAIREKIAEGKVRREDIFYCGKLWATNHVPEMVRPTLERTLRVLQLDYVDLYIIE
VPMAFKPGDEIYPRDENGKWLYHKSNLCATWEAMEACKDAGLVKSLGVSNFNRRQLELIL
NKPGLKHKPVSNQVECHPYFTQPKLLKFCQQHDIVITAYSPLGTSRNPIWVNVSSPPLLK
DALLNSLGKRYNKTAAQIVLRFNIQRGVVVIPKSFNLERIKENFQIFDFSLTEEEMKDIE
ALNKNVRFVELLMWRDHPEYPFHDEY
Enzyme 1 Number of Residues 326
Enzyme 1 Molecular Weight 37377
Enzyme 1 Theoretical pI 7.58
Enzyme 1 GO Classification
Function
  • catalytic activity
  • oxidoreductase activity
Process
—
Component
—
Enzyme 1 General Function Not Available
Enzyme 1 Specific Function Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7- alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4- cholesten-3-one can also act as substrates
Enzyme 1 Pathways
Enzyme 1 Reactions
  • 4,5beta-dihydrocortisone + NADP+ = cortisone + NADPH + H+
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 431857 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID P51857 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name AK1D1_HUMAN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >981 bp 
ATGGATCTCAGTGCTGCAAGTCACCGCATACCTCTAAGTGATGGAAACAGCATTCCCATC
ATCGGACTTGGTACCTACTCAGAACCTAAATCGACCCCTAAGGGAGCCTGTGCAACATCG
GTGAAGGTTGCTATTGACACAGGGTACCGACATATTGATGGGGCCTACATCTACCAAAAT
GAACACGAAGTTGGGGAGGCCATCAGGGAGAAGATAGCAGAAGGAAAGGTGCGGAGGGAA
GATATCTTCTACTGTGGAAAGCTATGGGCTACAAATCATGTCCCAGAGATGGTCCGCCCA
ACCCTGGAGAGGACACTCAGGGTCCTCCAGCTAGATTATGTGGATCTTTACATCATTGAA
GTACCCATGGCCTTTAAGCCAGGAGATGAAATATACCCTAGAGATGAGAATGGCAAATGG
TTATATCACAAGTCAAATCTGTGTGCCACTTGGGAGGCGATGGAAGCTTGCAAAGACGCT
GGCTTGGTGAAATCCCTGGGAGTGTCCAATTTTAACCGCAGGCAGCTGGAGCTCATCCTG
AACAAGCCAGGACTCAAACACAAGCCAGTCAGCAACCAGGTTGAGTGCCATCCGTATTTC
ACCCAGCCAAAACTCTTGAAATTTTGCCAACAACATGACATTGTCATTACTGCATATAGC
CCTTTGGGGACCAGTAGGAATCCAATCTGGGTGAATGTTTCTTCTCCACCTTTGTTAAAG
GATGCACTTCTAAACTCATTGGGGAAAAGGTACAATAAGACAGCAGCTCAAATTGTTTTG
CGTTTCAACATCCAGCGAGGGGTGGTTGTCATTCCTAAAAGCTTTAATCTTGAAAGGATC
AAAGAAAATTTTCAGATCTTTGACTTTTCTCTCACTGAAGAAGAAATGAAGGACATTGAA
GCCTTGAATAAAAATGTCCGCTTTGTAGAATTGCTCATGTGGCGCGATCATCCTGAATAC
CCATTTCATGATGAATACTGA
Enzyme 1 GenBank Gene ID Z28339 Link Image
Enzyme 1 GeneCard ID AKR1D1 Link Image
Enzyme 1 GenAtlas ID AKR1D1 Link Image
Enzyme 1 HGNC ID HGNC:388 Link Image
Enzyme 1 Chromosome Location 7
Enzyme 1 Locus 7q32-q33
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. Kondo KH, Kai MH, Setoguchi Y, Eggertsen G, Sjoblom P, Setoguchi T, Okuda KI, Bjorkhem I: Cloning and expression of cDNA of human delta 4-3-oxosteroid 5 beta-reductase and substrate specificity of the expressed enzyme. Eur J Biochem. 1994 Jan 15;219(1-2):357-63. [PubMed Link Image]
  2. Charbonneau A, The VL: Genomic organization of a human 5beta-reductase and its pseudogene and substrate selectivity of the expressed enzyme. Biochim Biophys Acta. 2001 Jan 26;1517(2):228-35. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available
Enzyme 2 [top]
Enzyme 2 ID 13005
Enzyme 2 Name Aldo-keto reductase family 1, member D1
Enzyme 2 Synonyms
  1. Delta 4-3-ketosteroid-5-beta- reductase
  2. Aldo-keto reductase family 1, member D1
  3. Delta 4-3- ketosteroid-5-beta-reductase, isoform CRA_a
Enzyme 2 Gene Name AKR1D1
Enzyme 2 Protein Sequence >Aldo-keto reductase family 1, member D1 
MDLSAASHRIPLSDGNSIPIIGLGTYSEPKSTPKGACATSVKVAIDTGYRHIDGAYIYQN
EHEVGEAIREKIAEGKVRREDIFYCGKLWATNHVPEMVRPTLERTLRVLQLDYVDLYIIE
VPMAFKPGDEIYPRDENGKWLYHKSNLCATWEAMEACKDAGLVKSLGVSNFNRRQLELIL
NKPGLKHKPVSNQVECHPYFTQPKLLKFCQQHDIVITAYSPLGTSRNPIWVNVSSPPLLK
DALLNSLGKRYNKTAAQIVLRFNIQRGVVVIPKSFNLERIKENFQIFDFSLTEEEMKDIE
ALNKNVRFVELLMWRDHPEYPFHDEY
Enzyme 2 Number of Residues 326
Enzyme 2 Molecular Weight 37377
Enzyme 2 Theoretical pI 7.58
Enzyme 2 GO Classification
Function
  • catalytic activity
  • oxidoreductase activity
Process
—
Component
—
Enzyme 2 General Function Not Available
Enzyme 2 Specific Function Not Available
Enzyme 2 Pathways Not Available
Enzyme 2 Reactions Not Available
Enzyme 2 Pfam Domain Function
Enzyme 2 Signals
  • None
Enzyme 2 Transmembrane Regions
  • None
Enzyme 2 Essentiality Not Available
Enzyme 2 GenBank ID Protein 120660002 Link Image
Enzyme 2 UniProtKB/Swiss-Prot ID A1L4P6 Link Image
Enzyme 2 UniProtKB/Swiss-Prot Entry Name A1L4P6_HUMAN Link Image
Enzyme 2 PDB ID Not Available
Enzyme 2 Cellular Location Not Available
Enzyme 2 Gene Sequence Not Available
Enzyme 2 GenBank Gene ID BC130625 Link Image
Enzyme 2 GeneCard ID A1L4P6 Link Image
Enzyme 2 GenAtlas ID AKR1D1 Link Image
Enzyme 2 HGNC ID HGNC:388 Link Image
Enzyme 2 Chromosome Location Not Available
Enzyme 2 Locus Not Available
Enzyme 2 SNPs SNPJam Report Link Image
Enzyme 2 General References
  1. Strausberg RL, Feingold EA, Grouse LH, Derge JG, Klausner RD, Collins FS, Wagner L, Shenmen CM, Schuler GD, Altschul SF, Zeeberg B, Buetow KH, Schaefer CF, Bhat NK, Hopkins RF, Jordan H, Moore T, Max SI, Wang J, Hsieh F, Diatchenko L, Marusina K, Farmer AA, Rubin GM, Hong L, Stapleton M, Soares MB, Bonaldo MF, Casavant TL, Scheetz TE, Brownstein MJ, Usdin TB, Toshiyuki S, Carninci P, Prange C, Raha SS, Loquellano NA, Peters GJ, Abramson RD, Mullahy SJ, Bosak SA, McEwan PJ, McKernan KJ, Malek JA, Gunaratne PH, Richards S, Worley KC, Hale S, Garcia AM, Gay LJ, Hulyk SW, Villalon DK, Muzny DM, Sodergren EJ, Lu X, Gibbs RA, Fahey J, Helton E, Ketteman M, Madan A, Rodrigues S, Sanchez A, Whiting M, Madan A, Young AC, Shevchenko Y, Bouffard GG, Blakesley RW, Touchman JW, Green ED, Dickson MC, Rodriguez AC, Grimwood J, Schmutz J, Myers RM, Butterfield YS, Krzywinski MI, Skalska U, Smailus DE, Schnerch A, Schein JE, Jones SJ, Marra MA: Generation and initial analysis of more than 15,000 full-length human and mouse cDNA sequences. Proc Natl Acad Sci U S A. 2002 Dec 24;99(26):16899-903. Epub 2002 Dec 11. [PubMed Link Image]
  2. Scherer SW, Cheung J, MacDonald JR, Osborne LR, Nakabayashi K, Herbrick JA, Carson AR, Parker-Katiraee L, Skaug J, Khaja R, Zhang J, Hudek AK, Li M, Haddad M, Duggan GE, Fernandez BA, Kanematsu E, Gentles S, Christopoulos CC, Choufani S, Kwasnicka D, Zheng XH, Lai Z, Nusskern D, Zhang Q, Gu Z, Lu F, Zeesman S, Nowaczyk MJ, Teshima I, Chitayat D, Shuman C, Weksberg R, Zackai EH, Grebe TA, Cox SR, Kirkpatrick SJ, Rahman N, Friedman JM, Heng HH, Pelicci PG, Lo-Coco F, Belloni E, Shaffer LG, Pober B, Morton CC, Gusella JF, Bruns GA, Korf BR, Quade BJ, Ligon AH, Ferguson H, Higgins AW, Leach NT, Herrick SR, Lemyre E, Farra CG, Kim HG, Summers AM, Gripp KW, Roberts W, Szatmari P, Winsor EJ, Grzeschik KH, Teebi A, Minassian BA, Kere J, Armengol L, Pujana MA, Estivill X, Wilson MD, Koop BF, Tosi S, Moore GE, Boright AP, Zlotorynski E, Kerem B, Kroisel PM, Petek E, Oscier DG, Mould SJ, Dohner H, Dohner K, Rommens JM, Vincent JB, Venter JC, Li PW, Mural RJ, Adams MD, Tsui LC: Human chromosome 7: DNA sequence and biology. Science. 2003 May 2;300(5620):767-72. Epub 2003 Apr 10. [PubMed Link Image]
Enzyme 2 Metabolite References Not Available